Wife’s Friend’s Sister

by Pilot2B

What’s your gender? Man
How old are you? 59
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? U.S.A
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Technology Manager and Retired Military Officer
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Spiritual
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Love Women and Sex
How many sexual partners have you had in your life (including oral sex)? 50
How many hookup stories have you here posted before? 4

Wife’s Friend’s Sister

How long ago did this hookup happen? 5 years ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? Just met that day

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? My wife and I were invited to spend a long weekend at a house in a gated resort community in Tennessee. The house was a rental property that belonged to our friend’s father-in-law. The house was huge on a lake in the woods, it was beautiful. Our friend’s sister Leslie met us there. She managed the rental properties for her father-in-law and was going to spend the weekend with us. Leslie was beautiful and about 45 at the time. She, in fact, was a model for women’s clothing. She wasn’t the skinny model type, she was about 5’5” and had a great figure with about 36C bra size. She had dirty blonde hair that was down over her shoulders. I normally prefer brunettes, that said she is gorgeous. My wife is totally different. She is very pretty a brunette with an olive complexion, an athletic build, 34b bra, and a nice heart shape bottom.

The first night we all sat on the deck talking and telling stories around the fire pit. I always enjoyed sitting by a fire. There is something earthy/primitive and romantic about it. Joining us were our married friends, their parents, and Leslie. Leslie was married, but her husband was not there. I had never met him but heard he was a “B” Musician that liked himself too much. Our friend’s father was a retired Colonel in the Marine Corps and pilot who flew combat flights in Vietnam. I am a retired Naval Officer and pilot. I always enjoy meeting and talking with Veterans. I asked the Colonel about his service and he opened up and told a few stories. I was very fortunate in that while I flew reconnaissance in the First Gulf War, I never was shot at and not had I lost any friends directly due to combat. Having read a good deal about the air war in Vietnam I can only imagine how difficult it was for the Colonel to open up and tell about the loss of a good friend on a mission.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We eventually headed to bed and I had to stop and use the bathroom as my wife walked down the stairs to our bedroom. As I came out of the bathroom, Leslie walked up to me thanked me for getting her Dad to open up and tell his stories as he had never done it before and was in his 70’s. She gave me a quick hug and kiss on the cheek and walked away.

As I said, this was a huge house with 3 levels, dens, porches, game rooms, and more. My wife went to bed and I was not ready yet, so I stayed in one of the dens and started to watch TV. About 15 minutes later, Leslie came into the den and sat down next to me on a sofa, asking if there was anything good on. I said something like the movie just started. I can’t remember the movie, but I was just sitting and watching a few minutes when Leslie moved closer to me and put her hand on my thigh. After a few minutes I did the same and she did not push me away. I started to rub her leg and slowly moved my hand down to the crotch of her panties; she was soaking wet. I slowly pushed her panties aside and started to move my fingers in and out. She had her head back and eyes closed enjoying the fingering.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? When I checked on my wife, she was deep asleep, so I went to the bedroom where Leslie was in the bed waiting. She had removed her sleepwear and was gloriously naked under the sheets. I climbed in next to her, rolled on my side, and kissed her for the first time. She kissed me back with total abandon. I finally was able to see her glorious breasts. I went down to kiss them and suckled on her nipple as I ran my fingers through her wet slit. I rolled Leslie on her back, climbed on top, and mounted her. She wrapped her legs around me as I penetrated deeper. I like slow penetrating sex with me pressuring a women’s clit at the downstroke. She was very wet and tight as she had no children. Apparently, Leslie liked it too as she was moaning in my ear that she was about to come and to come inside her when she orgasmed. I could feel her start to orgasm and I sunk in deep, ejaculating my cum inside her. I stayed inside her until I got soft, slipped out, and rolled off of her and onto my side. After a few minutes, Leslie said thank you, that was wonderful. She said we could talk more tomorrow but that I should get back to my wife. I went back to our bedroom and climbed into bed next to my wife.
Now it might seem odd, but I loved and still love my wife. Sex was good, but as she was going through menopause, she lost her sex drive and we had to use lubricant as she did not get wet easily. Having sex with a beautiful women 10 years my junior that had a strong sex drive was too good of an opportunity to pass up.

The next day, Leslie met me outside as I was getting ready to go for a hike by myself. She said that she really enjoyed last night and asked if I would like to meet her at one of the rental properties she managed later in the day. She knew that I had asked her for a pass for the Fitness Center nearby she belonged to. I normally work out almost every day so it would not appear abnormal to my wife. She gave me the address and location and time to meet her there. About 2 hours later, I got into my gym clothes and told everyone I was heading to the gym. Leslie had left about 15 minute earlier. When I got to the house at the address that Leslie gave me I walked to the front door and found it open with Leslie was sitting in the great room drinking a bottle of water. I walked over to her and took her into my arms to kiss her. She hugged me and kissed me back. She said that she wanted me again, but that we needed to talk. We sat down and proceeded to tell me that she was about to leave her husband, she was just saving enough money to make the jump. He had been cheating on her and he was basically a loser that played in a band and lived off of his wealthy father. Her only concern was that she did not want to break up my marriage. I assured her that I understood and appreciated it.

She then leaned over, kissed me, and took my hand leading me to a bedroom. She told me to get into bed and she did a slow striptease removing her top, shorts, bra, and panties. In the full daylight, she was a goddess; full breasts, rounded hips, and a flat stomach. She had a little blond landing strip above her slit, my favorite. She told me that she wanted to enjoy this and to lay down an let her take charge, I said yes Ma’am. She climbed into the bed reached over and took my semi-hard cock in her hand, leaned over and took the mushroom head into hear mouth. It felt great as she sucked on my tip using her tongue and cupping and massaging my balls. As she was sucking on me I was running my fingers through her puffy wet lips. When I was fully hard and ready Leslie climbed up put her leg over me, reached for my cock and rubbed it up and down her lips. When I was lubricated with her wetness she proceeded to slide all the way down until she bottomed out. After a few moments, she started to ride up and down on my cock, she would bottom out and grind her pubic bone against mine. It felt great and it took all my control not too cum too soon. Her beautiful breasts were dangling in my face so I took the opportunity to take turns sucking on each one. As we were alone this time, she was much more vocal with moaning and telling me how good it felt. I could tell she was getting close by her breathing and that her moans where getting closer together, suddenly she tensed up and told me she was cumming, I grabbed her bottom and pulled her to me and shot my load deep inside her.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Afterward, we laid together kissing. She said that I better get going to the gym, so we kissed, got dressed, and went on our way. Before I went home, we were able to talk and she told me thank you and that she did not regret our coupling and if we ever had the opportunity to meet up again, she would love to.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), It was easy / convenient

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Opportunity to have sex with a beautiful loving women.

What was the WORST thing about this hookup? We were not able to meet up again.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? I have only seen Leslie once since we hooked up at the wedding of our friend’s son. Sadly we were not able to talk or hook up. She was as beautiful as ever.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? It would be nice if it were more accepting in society to have more than one sexual partner at one time.

What do you think about the Casual Sex Project? Some great stories.

You have a hookup story to share? Submit it here!